Hydrogen Peroxide → HCID 14627784, compound

HRID 260606Notes

Reaction equation

HRID 260606 reaction equation
[OH:1]O.[OH-].[Na+].[CH3:5][O:6][C:7]1[CH:28]=[CH:27][C:10]([CH2:11][N:12]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:12]([CH2:22][CH2:23][CH2:24][C:25]([NH2:26])=[O:1])[CH2:11][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:28][CH:27]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 14627783HCID 14627783, compound

Product 1

HCID 14627784HCID 14627784, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Hydrogen peroxide (30% w/v; 5.67 ml ), tetra-n-butylammonium hydrogensulphate (1.70 g) and 5N aqueous sodium hydroxide (4 ml) were added successively to a stirred solution of 4-[N,N-bis-(4-methoxybenzyl)amino]butyronitrile (3.24 g) in dichloromethane (10 ml), with water cooling. The mixture was stirred vigorously at room temperature for 18 hours and dichloromethane (100 ml) was added. The layers were separated and the organic phase was washed with saturated aqueous sodium chloride (1×10 ml), dried (Na2SO4) and concentrated in vacuo to give an oil (4.71 g). The product was chromatographed on silica with eluant 20% ethyl acetate/toluene →ethyl acetate, and crystallised from diisopropyl ether at room temperature to give the title compound (2.21 g), m.p. 53°-54° C.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with saturated aqueous sodium chloride (1×10 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c06dec512bdb45bba9e24c497c2fed08
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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